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Site-selective chemical reactions by on-water surface sequential assembly

Author

Listed:
  • Anupam Prasoon

    (Technische Universität Dresden
    Max Planck Institute for Microstructure Physics)

  • Xiaoqing Yu

    (Max Planck Institute for Polymer Research)

  • Mike Hambsch

    (Technische Universität Dresden)

  • David Bodesheim

    (Technische Universität Dresden)

  • Kejun Liu

    (Technische Universität Dresden)

  • Angelica Zacarias

    (Max Planck Institute for Microstructure Physics)

  • Nguyen Ngan Nguyen

    (Technische Universität Dresden)

  • Takakazu Seki

    (Max Planck Institute for Polymer Research)

  • Aerzoo Dianat

    (Technische Universität Dresden)

  • Alexander Croy

    (Friedrich Schiller University Jena)

  • Gianaurelio Cuniberti

    (Technische Universität Dresden
    Technische Universität Dresden)

  • Philippe Fontaine

    (Synchrotron SOLEIL, L’Orme des Merisiers)

  • Yuki Nagata

    (Max Planck Institute for Polymer Research)

  • Stefan C. B. Mannsfeld

    (Technische Universität Dresden)

  • Renhao Dong

    (Technische Universität Dresden
    Shandong University)

  • Mischa Bonn

    (Max Planck Institute for Polymer Research)

  • Xinliang Feng

    (Technische Universität Dresden
    Max Planck Institute for Microstructure Physics)

Abstract

Controlling site-selectivity and reactivity in chemical reactions continues to be a key challenge in modern synthetic chemistry. Here, we demonstrate the discovery of site-selective chemical reactions on the water surface via a sequential assembly approach. A negatively charged surfactant monolayer on the water surface guides the electrostatically driven, epitaxial, and aligned assembly of reagent amino-substituted porphyrin molecules, resulting in a well-defined J-aggregated structure. This constrained geometry of the porphyrin molecules prompts the subsequent directional alignment of the perylenetetracarboxylic dianhydride reagent, enabling the selective formation of a one-sided imide bond between porphyrin and reagent. Surface-specific in-situ spectroscopies reveal the underlying mechanism of the dynamic interface that promotes multilayer growth of the site-selective imide product. The site-selective reaction on the water surface is further demonstrated by three reversible and irreversible chemical reactions, such as imide-, imine-, and 1, 3-diazole (imidazole)- bonds involving porphyrin molecules. This unique sequential assembly approach enables site-selective chemical reactions that can bring on-water surface synthesis to the forefront of modern organic chemistry.

Suggested Citation

  • Anupam Prasoon & Xiaoqing Yu & Mike Hambsch & David Bodesheim & Kejun Liu & Angelica Zacarias & Nguyen Ngan Nguyen & Takakazu Seki & Aerzoo Dianat & Alexander Croy & Gianaurelio Cuniberti & Philippe F, 2023. "Site-selective chemical reactions by on-water surface sequential assembly," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-44129-7
    DOI: 10.1038/s41467-023-44129-7
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    References listed on IDEAS

    as
    1. Jing Liu & Qiwei Chen & Kang Cai & Jie Li & Yaru Li & Xiao Yang & Yajie Zhang & Yongfeng Wang & Hao Tang & Dahui Zhao & Kai Wu, 2019. "Stepwise on-surface dissymmetric reaction to construct binodal organometallic network," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    2. Helen M. Burke & Lauren McSweeney & Eoin M. Scanlan, 2017. "Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology," Nature Communications, Nature, vol. 8(1), pages 1-16, August.
    3. Naoki Yoneda & Yuki Fujii & Akira Matsumoto & Keisuke Asano & Seijiro Matsubara, 2017. "Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins," Nature Communications, Nature, vol. 8(1), pages 1-7, December.
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